In case I wasn't explaining things very well, here's a diagram of what I am trying to achieve:
You explained it right, you didn't understand Charlies response right.
You have two choices, well three really, setup a proxy pass
or add an entry to SME's host file.
The third we won't get involved in at this point.
http://localhost:8886
That works because there is a default host entry for localhost.
You just tagged the port to it.
http://my.smeserver.address.com:8886
Where is DNS going to find
my.smeserver.address.com, sure can't pull it out of thin air.
I would venture a guess that the forward from client to dev server will not be using the tunnel, as much as you think it is.
As mush as you think that your setting up a secure network, you've actually created a network security vulnerability.
AKA foobar Network Config.
Just because something works or (you think it works)...... doesn't mean it's not a network security vulnerability.
Sorry....reality is reality no matter how you butter it up.
However I won't try to deter you from the learning experience or did I already??
Nice Visio drawing, be nice if everyone did that when they post their issues here.
A+ for the drawing, F for network setup.
One out of two ain't bad.
However you only get an @ a boy for straight A's.
hth